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The Real Pirates of the Caribbean and their flags

Typical Skull and Crossbones
or "Jolly Rodger" Flag

     The classic era of piracy was in the Caribbean, between 1650 and the mid-1720s. The European powers of the day were busy developing their colonial empires at this time and the wealth discovered in the New World was there for the taking, since much of it travel by ship. Much of the piracy was actually carried out by the European powers whose merchant ships strangely were armed to the hilt and prowled the Caribbean looking for victims, although there were real pirates also in the mix. Whatever the Pirates true nature, they usually lowered their true colors and stored them safely in a chest, and raised their particular pirate "Jolly Rodger" to hide their true identity.

The French Buccaneers

     The French buccaneers were first, establishing bases of operation on northern Hispaniola as early as 1625, but Spanish efforts to wipe out forced them to migrate from Hispaniola to the more defensible offshore island of Tortuga. This began an era of various royal governors providing safe ports for pirates and similarly provided privateering commissions for them to prey on rival shipping. The Tortuga buccaneer Pierre Le Grand was the first to attack Spanish galleons making the return voyages to Spain with their riches from their New World holdings. This began a semi-competitive competition between the colonizing powers to cripple their rival's shipping. The growth of buccaneering from French Tortuga was augmented by the English capture of Jamaica from Spain in 1655.

The English Privateers

     The early English governors of Jamaica freely granted letters of marque to both the French buccaneers and to their own British commanders, while the growth of Port Royal provided these raiders with a far more profitable and enjoyable place to sell their booty. The new French governor of Tortuga, Bertrand d'Ogeron, similarly provided privateering commissions both to his own colonists and to English cutthroats from Port Royal. These conditions brought Caribbean buccaneering to its "Golden Age", so to speak, with this unofficial agreement between the French and English to have their "privateers" plunder the "Spanish Main."

The "Golden Age" of Caribbean Buccaneering

     In this age of political and moral decay, many pirate superstars were born, and their names would soon become enshrined in infamy. The voyage of the Golden Hind under Francis Drake and his plundering of Spanish ports along the Pacific Coast of South America comes to mind. Henry Every's capture of the Grand Mughal ship Ganj-i-Sawai in 1695 stands as one of the most profitable pirate raids ever perpetrated. Bartholomew Roberts would become the pirate with most "captures" during this Golden Age of Piracy. He is also remembered for hanging the governor of Martinique from the yardarm of his ship.
     A new phase of piracy began in the 1690s as English pirates began to look beyond the Caribbean for their treasures. In the 1690s, with the fall of Britain's Stuart kings the traditional rivalry between Britain and France ending the profitable collaboration between English Jamaica and French Tortuga. Some pirates also began operating out of New England and the Middle Colonies, targeted Spain's remoter Pacific coast colonies, even as far away as the Indian Ocean. This set the stage for the famous pirates, Thomas Tew, Henry Every, Robert Culliford, William Kidd, and possibly Captain James Misson if he existed.
     In the following years, the Caribbean colonial governors began to discard their traditional policy of allowing European wars to "continue" in the Caribbean regardless of peace treaties signed in Europe, and they began to only give commissions for "privateers" in actual wartime. By this time Maracaibo alone had been sacked three times, while RÍo de la Hacha had been raided five times and Tolú eight.
     The shipping traffic between Africa, the Caribbean, and Europe, including the slave trade, began to soar in the 18th Century. Known as the triangular trade, it became a rich target for piracy. As living conditions among merchant sailors become so poor, many sailors began to prefer a freer existence as a pirate. It is said that merchant sailors suffered from mortality rates as high or higher than the slaves being transported. The increased volume of shipping traffic also would sustain the larger body of brigands preying upon it. Among the most infamous Caribbean pirates of this time were Edward Teach, or Blackbeard, Calico Jack Rackham and Bartholomew Roberts.

The Beginning of the End

     In 1715, a group of pirates launched a major raid on Spanish divers trying to recover gold from a sunken treasure galleon near Florida. Led by Henry Jennings, and a group of English ex-privateers (Charles Vane, Samuel Bellamy, and Edward England), the attack was successful, but resulted in the governor of Jamaica refused to allow Jennings and his cohorts to spend their loot on his island. With Kingston and Port Royal now closed to them as the chief market for fenced plunder, the pirates temporarily founded a new base at Nassau in the Bahamas. Nassau would house these pirates for several years, before a new royal governor would end the practice. Christopher Condent was especially active off the coast of Brazil, Africa, and the Indian Ocean from 1718 to 1720. He is one of the few famous pirates to successfully retire from piracy as a wealthy man. By 1730, most of these pirates were eventually hunted down by the Royal Navy and killed or captured as several battles fought between the brigands and the colonial powers on both land and sea ended this particular threat.

The Last Buccaneers

     Piracy in the Caribbean continued to decline for the next several decades and by the 1810s, although many pirates still roamed the waters, they were not as "bold" as their predecessors. The most successful pirates of this declining era were Jean Lafitte and Roberto Cofresi. In fact, Lafitte is considered by many to be the last buccaneer. He maintained a private army of pirates and fleet of pirate ships in bases in and around the Gulf of Mexico. Lafitte and his men would later participated in the War of 1812 at the Battle of New Orleans fighting the British along side of Andrew Jackson's forces. Cofresi's base was in Mona Island, Puerto Rico, from where he disrupted the commerce throughout the region. He became the last major target of an international anti-piracy operation.
     Many of the flags shown below are drawn from vague written descriptions or unclear renderings, while others are most likely modern flights of fancy, or manufacturer speculations. However, all exist in reality today and are being sold as historical flags.

Reported Flags of Pirates
Both Real and Fanciful

Flag of Black Bart Roberts
Second Flag of Black Bart Roger
Flag of Christopher Moody
Flag of Jean Thomas Dulaien ✱
Flag of Edward England
Flag of Edward Lowe
Flag of Edward Teach
Flag of Emanuel Wynne
Flag of Henry Avery (black)
Flag of Henry Avery (red)
Flag of Jack Rackham
Flag of John Quelch
Second Flag of John Quelch
Flag of Richard Worley
Second Flag of Richard Worley
Flag of Stede Bonnett
Flag of Thomas Tew
Flag of Samuel Bellamy
Flag of Christopher Condent
Flag of Walter Kennedy ✱
The Cartagena Republic
Flag of Jean LaFitte
Pirate Republic of Libertaria
(non-Caribbean French Pirate Myth)

According to legend, a colony was
founded in the late 17th century in
Madagascar by pirates under the
leadership of Captain James Misson.
They used a plain white flag with red
lettering stating "for God and liberty".
image by Olivier Touzeau
Flag of Libertaria #1
by António Martins-Tuválkin
Speculative drawings by vexillologist
based on written descriptions
Flag of Libertaria #2
by Olivier Touzeau

✱ The pirates Walter Kennedy and Jean Thomas Dulaien reportably used the same or similar flag

Please note: Many of the flags illustrated on this page are undocumented and most likely modern fantasy flags.
I've seen quite a few flying from docked vessels in yacht harbors around the country.